Winter Date Night Outfits: What to Wear for Dinner, Drinks and a First Date

For a winter date, wear one warm main piece, such as a long-sleeve dress or a set with a fine knit underneath, then add black tights, boots you can walk in and a long coat that covers your hemline. Choose the dress for the room you will spend the evening in, and the coat and shoes for the walk there and back. Below is one complete outfit for each kind of date, from dinner to the theatre, with the coat and shoes already worked out. For more dresses to start from, see going-out dresses.

What to wear on a dinner date in winter

At dinner you sit for two hours and the table hides everything below the waist, so the top half of the outfit does most of the work. Long sleeves matter more than length: they let you hand over your coat at the door and still be comfortable at a table by the window.

The Noor Lace-Trim Long Sleeve Mini Dress is a good example. It is black and slim, with long sleeves, a V-neck and lace trim, so it looks finished on its own. Wear it with 40 denier black tights and the Feliz Knee High Leather-Look Boots, which have a chunky sole and a 6 cm block heel. With knee boots and dark tights, only a little leg shows between hem and boot, which is what makes a mini sensible in December. Finish with a coat that falls well past the hem, from long coats, and a small shoulder bag.

What to wear for drinks at a bar in winter

A bar is darker, louder and usually warmer than a restaurant, and you may be standing most of the night. That makes it the place for shine and for a set. The Helena Sequin Leopard Two-Piece Set pairs a fitted top with a low-rise bodycon skirt, in a sequin leopard print that catches the light as you move.

To wear it in winter, put a fine black roll-neck under the top, then keep everything else black: opaque tights, heeled ankle boots and a jacket from faux leather jackets. The print stays the only loud thing in the outfit, which is why it looks deliberate. If the walk is longer than ten minutes or it is below freezing, swap the jacket for your long coat. There are more two-piece options in going-out sets.

What to wear on a first date in winter

A first date is usually a drink or a coffee, sometimes followed by dinner if it goes well, so dress for the middle: smarter than your weekend clothes, less than a party. A long-sleeve dress in a pattern or a colour does this better than black, because it looks chosen without looking formal.

The Hedda Plaid Long Sleeve Mini Dress comes in burgundy plaid, with a boat neck, button detail and a flared skirt. Wear it with 60 denier black tights, loafers or flat knee boots from boots and loafers, and a short jacket or a long coat in a plain colour, so the plaid stays the focus. Flat shoes are a good call here: you may end up walking to a second place, and you will be more relaxed if your feet are. There is more on short hemlines in the cold in can you wear a mini dress in winter.

What to wear on an outdoor winter date

A winter market, an ice rink or a long walk changes the priorities. You are outside for hours, on your feet, with your hands full. Trousers are the warmest choice: straight trousers or dark jeans, a fine roll-neck under a heavier sweater, a long coat buttoned to the top, flat boots with a grip sole, gloves and a scarf. A crossbody bag keeps both hands free for a hot drink.

If you would rather wear a dress, choose a midi from knit dresses with 80 denier tights and flat knee boots, so no skin is exposed between hem and boot. For more cold-weather combinations, see eight winter outfits that actually work.

What to wear to the theatre or for cocktails

A dressier evening needs one sharp piece and sheer tights. The Maren Deep V-Neck Long Sleeve Blazer Dress is a black crepe dress cut like a tailored jacket, with long sleeves, flap pockets and a rounded mini skirt. It holds its shape in a theatre seat because the structure sits in the top half. Wear it with 15 denier black tights and a pointed ankle boot, or a heel you can stand in during the interval.

Over it, the Claudine Long Belted High Collar Coat in black or grey covers the dress completely, and the high collar does the job of a scarf. Carry the Jasmin Embossed Clutch, a top-handle clutch in embossed vegan leather with room for a phone, cards and a lipstick; the burgundy version looks good against black. There are more in evening bags. If you prefer a softer fabric, a slip from satin dresses works the same way with a fine black cardigan over it, and black dresses has more tailored shapes.

How to stay warm on a winter date without bulk

• Layer thin, not thick. A fine roll-neck or a thermal vest under a dress adds more warmth than a chunky sweater over it, and nobody sees it.
• Choose tights by temperature. 15 to 20 denier for a short walk and a warm room, 40 denier for most evenings, 60 to 80 denier or fleece-lined tights when it is below freezing. Black tights in any weight make mini dresses wearable through winter.
• Let the coat carry the warmth. A long coat that covers your hemline keeps your legs warm outside, and it comes off as soon as you sit down, so the outfit underneath can stay light.
• Dress for the walk between places. If dinner is followed by a bar, wear a block heel under 7 cm or a lug sole, keep gloves in your coat pocket and choose a bag with a strap. Leave open-toe shoes and suede-look heels at home if the pavements are wet.

Common questions

What should I wear on a first date in winter?
Something one step smarter than your everyday clothes: a long-sleeve dress with opaque tights and loafers or flat boots, or good trousers with a fine knit. Add a coat you are happy to be seen in, since it is the first thing your date will see.

Can you wear a dress on a date in winter?
Yes. Choose long sleeves, wear tights in a weight that suits the temperature, and add knee boots and a coat that is longer than the dress.

What shoes should I wear on a winter date?
Knee or ankle boots with a block heel or lug sole for most dates, loafers for a casual one, and a slim heel only when you will not walk far.

What do you wear to dinner when it is too cold for a dress?
Wide-leg trousers with a fine knit or a silky top, heeled ankle boots and a long coat. A matching trouser set does the same job in one decision.

There are more dresses for an evening out in going-out dresses, from long-sleeve minis to maxi dresses. For two pieces that make the outfit in one go, see going-out sets, and finish with a coat from long coats.